The Politics of Competitive Board Gaming Amongst Friends is a short documentary by Jay Cheel whose subject is summed up by its title. You can see other short films by Cheel at his website. The main protagonist of the doc, Gerry Eng, a.k.a. Reed Farrington, has been the subject of many Cheel films, such as Cooking with Gerry, Cooking with Gerry #2, Poutine, A Very Gerry X-Mas and Reed's House.
Maria Bamford's One-Hour Homemade Christmas Special! by Maria Bamford, stand-up comic and pretty much a native speaker in Pretend Tiger. FYI, if you've heard some of those jokes before... it's a gift! She made it for us, for Christmas, to celebrate her success at selling out this year.